2-hydroxymethyl-6-methyl-cyclohexanone | 90112-65-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-hydroxymethyl-6-methyl-cyclohexanone
• 英文别名: 2-hydroxymethyl-6-methylcyclohexanone；1-Methyl-3-hydroxymethyl-cyclohexanon-(2)；2-(Hydroxymethyl)-6-methylcyclohexan-1-one
• CAS: 90112-65-5
• 化学式: C₈H₁₄O₂
• 分子量: 142.198
• InChiKey: SZFWNTXXVYETLW-UHFFFAOYSA-N

物化性质

• 沸点：
  89-92 °C(Press: 4.5 Torr)
• 密度：
  1.004±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-Hydroxymethylen-3-methylcyclohexanon-(2) 在 镍 氢气 作用下， 以 乙醇 为溶剂， 生成 2-hydroxymethyl-6-methyl-cyclohexanone
  参考文献：
  名称：

  Dallacker,F. et al., Justus Liebigs Annalen der Chemie, 1961, vol. 647, p. 23 - 36

  摘要：

  DOI：

文献信息

• Stabilization of reactive aldehydes by complexation with methylaluminum bis(2,6-diphenylphenoxide) and their synthetic application
  作者：Keiji Maruoka、Arnel B. Concepcion、Noriaki Murase、Masataka Oishi、Naoki Hirayama、Hisashi Yamamoto

  DOI：10.1021/ja00063a013

  日期：1993.5

  Reactive aldehydes such as formaldehyde and α-chloro aldehydes can be successfully generated by treatment of readily available trioxane and α-chloro aldehyde trimers, respectively, with methylaluminum bis(2,6-diphenylphenoxide) (MAPH), and stabilized as their 1:1 coordination complexes with MAPH. The resulting CH 2 =O.MAPH complex reacts with a variety of olefins to furnish ene-reaction products with

  通过分别用甲基铝双（2,6-二苯酚）（MAPH）处理容易获得的三恶烷和 α-氯醛三聚体，可以成功地生成反应性醛，如甲醛和 α-氯醛，并以 1:1与 MAPH 的配位配合物。所得的 CH 2 =O.MAPH 复合物与多种烯烃反应，提供具有优异区域选择性和立体选择性的烯反应产物。此外，该配合物以及 α-氯醛-MAPH 配合物可分别用作气态甲醛和活性 α-氯醛的稳定来源，用于各种碳负离子（有机金属化合物、烯醇化物等）的亲核加成。
• Lanthanide Trifluoromethanesulfonates as Stable Lewis Acids in Aqueous Media. Yb(OTf)₃Catalyzed Hydroxymethylation Reaction of Silyl Enol Ethers with Commercial Formaldehyde Solution
  作者：Shu Kobayashi

  DOI：10.1246/cl.1991.2187

  日期：1991.12

  Silyl enol ethers smoothly react with commercial formaldehyde solution to give the corresponding hydroxymethylated adducts in high yields by the promotion of a catalytic amount of ytterbium(III) triflate (Yb(OTf)3), which is a stable Lewis acid in aqueous media. Other lanthanide triflates are also found to be effective.

  通过催化量的三氟甲磺酸镱 (III) (Yb(OTf)3)（一种在水性介质中是稳定的路易斯酸），甲硅烷基烯醇醚与商业甲醛溶液顺利反应，以高产率得到相应的羟甲基化加合物。其他镧系元素三氟甲磺酸盐也被发现是有效的。
• Aldol Synthesis with an Aqueous Solution of Formalin
  作者：Hisashi Yamamoto、Nobuko Ozasa、Manabu Wadamoto、Kazuaki Ishihara

  DOI：10.1055/s-2003-42089

  日期：——

  With an aqueous solution of formalin, aldol reaction of trimethylsilyl enol ether proceeds moderately using tetrabutyl­ammonium fluoride (TBAF). Furthermore, catalytic asymmetric hydroxymethylation with trimethoxysilyl enol ether using water tolerant (R)-BINAP-AgOTf as Lewis acid and KF as Lewis base has been achieved in aqueous media.

  在福尔马林水溶液中，使用四丁基氟化铵（TBAF）可温和地进行三甲基硅基烯醇醚的醛醇反应。此外，以耐水的 (R)-BINAP-AgOTf 为路易斯酸，KF 为路易斯碱，在水介质中实现了与三甲氧基硅基烯醇醚的催化不对称羟甲基化反应。
• Noxious-insect repellent
  申请人：Kanebo, Ltd.

  公开号：US20040091515A1

  公开（公告）日：2004-05-13

  Disclosed is a method of repelling noxious insects comprising the step of exposing said noxious insects to a composition containing from 0.1 to 90 wt. %, based on the total weight of the composition, of at least one of 2-(1-hydroxyalkyl)cycloalkanones represented by the following formula 11: 1 wherein n is an integer of 3-10, R 1 is hydrogen or a straight-chain saturated hydrocarbon radical having 1-6 carbon atoms; R 2 is hydrogen or methyl group and R m ′ represents m′ of the same or different, straight-chain or branched, saturated or unsaturated, hydrocarbon radicals R which, as a substituent group, can be bonded to carbocyclic atoms; m′ is an integer of 0-8, provided that m′ should be at least 2 when n is at least 4 and both the R 1 and R 2 are alkyl groups; the sum of the carbon atoms of R m ′ does not exceed 12; and, further, when n is 4, R may be an isopropylidene group which intramolecularly bridges between the third and sixth carbocyclic atoms.

  本发明涉及一种驱除有害昆虫的方法，其步骤包括将所述有害昆虫暴露于含有以下化合物之一的组成物中，所述化合物占组成物总重量的0.1至90重量％：2-（1-羟基烷基）环烷酮，其化学式为11:1，其中n为3-10的整数，R1为氢或具有1-6个碳原子的直链饱和碳氢基团，R2为氢或甲基基团，Rm'代表相同或不同的m'，直链或支链，饱和或不饱和，碳氢基团R，作为取代基团，可以与环状碳原子结合；m'为0-8的整数，但当n至少为4且R1和R2均为烷基时，m'应至少为2；Rm'的碳原子总数不超过12；当n为4时，R可以是一个异丙亚甲基基团，其在第三个和第六个环状碳原子之间形成分子内桥接。
• Lanthanide Triflates as Water-Tolerant Lewis Acids. Activation of Commercial Formaldehyde Solution and Use in the Aldol Reaction of Silyl Enol Ethers with Aldehydes in Aqueous Media
  作者：Shu Kobayashi、Iwao Hachiya

  DOI：10.1021/jo00092a017

  日期：1994.7

  Lanthanide trifluoromethanesulfonates (triflates), especially ytterbium triflate (Yb(OTf)(3)), were found to be stable Lewis acids in water. In the presence of a catalytic amount of lanthanide triflate, formaldehyde in water solution (commercial formaldehyde solution) was activated and the hydroxymethylation reaction of silyl enol ethers proceeded smoothly. Lanthanide triflates were also quite effective in the aldol reaction of silyl enol ethers with aldehydes in aqueous media, and water-soluble aldehydes such as acetaldehyde, acrolein, and chloroacetaldehyde could be employed for direct use. Moreover, in all these reactions, lanthanide triflates were quantitatively recovered after the reactions were completed and could be reused.